Table 1.
1H and 13C-NMR data for compounds 1 and 2 (600 and 150 MHz, DMSO-d6, δ ppm).
| No. | 1 | 2 | ||||
|---|---|---|---|---|---|---|
| δC | δH (mult, J in Hz) | HMBC | δC | δH (mult, J in Hz) | HMBC | |
| 2 | 155.7 | 155.7 | ||||
| 3 | 133.1 | 133.3 | ||||
| 4 | 177.4 | 177.4 | ||||
| 5 | 160.7 | OH (12.66) | 160.9 | 12.65 (OH) | ||
| 6 | 99.3 | 6.32(d, 2.4) | C-5, C-7, C-8 | 99.2 | 6.38 (d, 1.8) | C-5, 8, 10 |
| 7 | 161.5 | 161.4 | ||||
| 8 | 93.8 | 6.63(d, 2.4) | C-7, C-9, C-10 | 94.1 | 6.69 (d, 1.8) | C-6, 7, 9, 10 |
| 9 | 155.7 | 155.6 | ||||
| 10 | 105.5 | 105.5 | ||||
| 1ꞌ | 120.9 | 122.2 | ||||
| 2ꞌ | 130.9 | 8.01 (d, 9) | C-2, C-4ꞌ | 115.8 | 7.50 (d, 1.8) | C-1ꞌ, 3ꞌ, 4ꞌ, 2 |
| 3ꞌ | 115.4 | 6.89 (d, 9 ) | C-4ꞌ | 144.9 | ||
| 4ꞌ | 156.0 | OH (s, 10.18) | 148.8 | |||
| 5ꞌ | 115.4 | 6.89 (d, 9) | C-4ꞌ | 115.2 | 6.82 (d, 8.4) | C-3ꞌ, 4ꞌ, 6ꞌ |
| 6ꞌ | 130.9 | 8.01 (d, 9) | C-2ꞌ | 120.7 | 7.65 (dd, 8.4, 1.8) | C-2ꞌ, 4ꞌ, 5ꞌ, 2 |
| 1ꞌꞌ | 98.5 | 5.50 (d, 1.2) | C-7, 3ꞌꞌ | 98.4 | 5.54 (s) | C-7, 2ꞌꞌ |
| 2ꞌꞌ | 69.8 | 3.87 (br. m) | C-3ꞌꞌ, 4ꞌꞌ | 69.8 | 3.86 (br. s) | C-5ꞌꞌ |
| 3ꞌꞌ | 70.2 | 3.63 (m) | 70.3 | 3.65 (dd, 3.0, 9.0 ) | ||
| 4ꞌꞌ | 71.6 | 3.31 (m) | C-3ꞌꞌ | 71.6 | 3.33 (m) | C-2ꞌꞌ, 6ꞌꞌ |
| 5ꞌꞌ | 70.0 | 3.43 (m) | C-4ꞌꞌ, 6ꞌꞌ | 70.1 | 3.45 (m) | C-3ꞌꞌ, 4ꞌꞌ |
| 6ꞌꞌ | 18.0 | 1.13 (3H, d, 6.0) | C-4ꞌꞌ, 5ꞌꞌ | 17.9 | 1.14 (d, 6.0) | C-4ꞌꞌ, 5ꞌꞌ |
| 1ꞌꞌꞌ | 97.0 | 5.81 (d, J = 7.8) | C-3, 2ꞌꞌꞌ, 5ꞌꞌꞌ | 98.5 | 5.59 (d, 7.8 ) | C-3 |
| 2ꞌꞌꞌ | 77.4 | 3.77 (dd, 9.6, 7.8) | C-5ꞌꞌꞌ, 1ꞌꞌꞌ | 72.9 | 3.61 (dd, 9.0, 7.8) | C-3ꞌꞌꞌ |
| 3ꞌꞌꞌ | 75.6 | 3.34 (m) | C-2ꞌꞌꞌ | 81.9 | 3.76 (dd, 9.0, 4.0) | C-1ꞌꞌꞌꞌ, C-1ꞌꞌꞌ, C-2ꞌꞌꞌ |
| 4ꞌꞌꞌ | 68.1 | 3.65 (m) | C-5ꞌꞌꞌ | 67.5 | 3.68 (dd, 4.0, 3.0) | C-ꞌꞌꞌ, 3ꞌꞌꞌ |
| 5ꞌꞌꞌ | 72.0 | 3.62 (m) | C-6ꞌꞌꞌ | 75.8 | 3.30 (m) | C-1ꞌꞌꞌ, 4ꞌꞌꞌ, 6ꞌꞌꞌ |
| 6ꞌꞌꞌ | 61.0 | 3.72 (m) 3.51 (m) |
59.9 | 3.23 (m), 3.38 (m) | C-4ꞌꞌꞌ, 5ꞌꞌꞌ | |
| 1ꞌꞌꞌꞌ | 98.3 | 5.08 (d, 7.8) | C-2ꞌꞌꞌ | 105.0 | 4.59 (d, 7.8 ) | C-3ꞌꞌꞌ, 2ꞌꞌꞌꞌ, 5ꞌꞌꞌꞌ |
| 2ꞌꞌꞌꞌ | 73.5 | 4.69 (dd, 9.0, 7.8) | C-1ꞌꞌꞌꞌ, 3ꞌꞌꞌꞌ, 1ꞌꞌꞌꞌꞌ | 74.8 | 3.15 (dd, 9.0, 7.8 ) | C-1ꞌꞌꞌꞌ, 5ꞌꞌꞌꞌ |
| 3ꞌꞌꞌꞌ | 74.4 | 3.45 (m) | C-2ꞌꞌꞌꞌ, 4ꞌꞌꞌꞌ | 74.0 | 3.56 (dd, 9.0, 7.2) | C-4ꞌꞌꞌꞌ |
| 4ꞌꞌꞌꞌ | 70.4 | 3.23 (m) | C-3ꞌꞌꞌꞌ, 5ꞌꞌꞌꞌ | 70.0 | 3.23 (m) | C-5ꞌꞌꞌꞌ |
| 5ꞌꞌꞌꞌ | 76.6 | 3.28 (m) | C-4ꞌꞌꞌꞌ | 76.0 | 3.30 | C-4ꞌꞌꞌꞌ |
| 6ꞌꞌꞌꞌ | 59.9 | 3.23 (m) 3.36 (m) |
C-3ꞌꞌꞌꞌ, 5ꞌꞌꞌꞌ | 64.2 | 4.30 (dd, 6.0, 12.0) 4.40 (br. d, 12.0) |
C-1ꞌꞌꞌꞌꞌ, C-3ꞌꞌꞌꞌ C-1ꞌꞌꞌꞌꞌ, 3ꞌꞌꞌꞌ |
| 1ꞌꞌꞌꞌꞌ | 165.7 | 165.4 | ||||
| 2ꞌꞌꞌꞌꞌ | 115.2 | 6.31 (d, 16.2) | C-4ꞌꞌꞌꞌꞌ, C-1ꞌꞌꞌꞌꞌ | 129.4 | ||
| 3ꞌꞌꞌꞌꞌ | 144.5 | 7.37 (d, 16.2) | C-1ꞌꞌꞌꞌꞌ, 2ꞌꞌꞌꞌꞌ, 4ꞌꞌꞌꞌꞌ, 5ꞌꞌꞌꞌꞌ, 9ꞌꞌꞌꞌꞌ | 128.7 | 7.69 (d, 7.2) | C-1ꞌꞌꞌꞌꞌ, 5ꞌꞌꞌꞌꞌ |
| 4ꞌꞌꞌꞌꞌ | 124.3 | 128.1 | 7.20 (t, 7.2) | C-1ꞌꞌꞌꞌꞌ, 3ꞌꞌꞌꞌꞌ, 7ꞌꞌꞌꞌꞌ, 5ꞌꞌꞌꞌꞌ | ||
| 5ꞌꞌꞌꞌꞌ | 105.4 | 6.70 (s) | C-3ꞌꞌꞌꞌꞌ, 4ꞌꞌꞌꞌꞌ 6ꞌꞌꞌꞌꞌ, 7ꞌꞌꞌꞌꞌ, 8ꞌꞌꞌꞌꞌ | 132.7 | 7.38 (t, 7.2) | C-3ꞌꞌꞌꞌꞌ, 7ꞌꞌꞌꞌꞌ |
| 6ꞌꞌꞌꞌꞌ | 147.7 | 128.1 | 7.20 (t, 7.2 ) | C-1ꞌꞌꞌꞌꞌ, 3ꞌꞌꞌꞌꞌ, 7ꞌꞌꞌꞌꞌ, 5ꞌꞌꞌꞌꞌ | ||
| 7ꞌꞌꞌꞌꞌ | 137.9 | 8.75 (OH) | 128.7 | 7.69 (d, 7.2) | C-1ꞌꞌꞌꞌꞌ, 5ꞌꞌꞌꞌꞌ | |
| 8ꞌꞌꞌꞌꞌ | 147.7 | |||||
| 9ꞌꞌꞌꞌꞌ | 105.4 | 6.70 (s) | C-3ꞌꞌꞌꞌꞌ, 4ꞌꞌꞌꞌꞌ, 6ꞌꞌꞌꞌꞌ, 7ꞌꞌꞌꞌꞌ, 8ꞌꞌꞌꞌꞌ | |||
| CH3O | 55.8 | 3.72 (s) × 2 | C-5ꞌꞌꞌꞌꞌ, 6ꞌꞌꞌꞌꞌ, 8ꞌꞌꞌꞌꞌ, 9ꞌꞌꞌꞌꞌ | |||